GB840725A - Process of perfluoroalkylating aromatic compounds - Google Patents

Process of perfluoroalkylating aromatic compounds

Info

Publication number
GB840725A
GB840725A GB24567/56A GB2456756A GB840725A GB 840725 A GB840725 A GB 840725A GB 24567/56 A GB24567/56 A GB 24567/56A GB 2456756 A GB2456756 A GB 2456756A GB 840725 A GB840725 A GB 840725A
Authority
GB
United Kingdom
Prior art keywords
dye
perfluoroheptyl
heated
carbon atoms
iodide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB24567/56A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Co
Original Assignee
Minnesota Mining and Manufacturing Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co
Publication of GB840725A publication Critical patent/GB840725A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/22—Dibenzanthrones; Isodibenzanthrones
    • C09B3/30—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/40—Pyranthrones
    • C09B3/44—Preparation from starting materials already containing the pyranthrone nucleus
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
    • C09B47/14—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid dyes
    • C09B7/10—Bis-thionapthene indigos

Abstract

Alkyd-type resins, which are both oleophobic and hydrophobic, are prepared from perfluoroalkylated phthalic anhydrides in which the perfluoroalkyl group contains 3-12 carbon atoms. In an example, perfluoroheptylphthalic anhydride and glycerol are heated together in the molar ratio 3:2, and a solution of the product in a fluorine-containing solvent is coated on glass to give a film which hardens on heating.ALSO:The invention comprises perfluoroalkylated aromatic compounds and a process of preparing them by the action of a perfluoroalkyl monoiodide having 3-12 carbon atoms in the molecule on an aromatic compound having a replaceable nuclear hydrogen atom, at 200-350 DEG C. In examples benzene is heated with perfluoropropyl-iodide, and perfluoroheptyl-iodide, to give perfluoropropyl or perfluoroheptyl benzene with some diperfluoro-derivatives and isomeric products; toluene, naphthalene, benzonitrile, bromobenzene, iodobenzene, and phthalic anhydride, are also treated with perfluoroheptyl iodide to give the corresponding perfluoroheptyl products.ALSO:The invention comprises aromatic dyes containing nuclear-attached perfluoroalkyl chains of 3-12 carbon atoms, which are soluble in fluorinated solvents but insoluble in hydrocarbon solvents, and which contain at least about 50% chlorine and are stable at temperatures at least as high as 200 DEG C., and a process for perfluoroalkylating aromatic dyes, containing a replaceable hydrogen atom attached to an aromatic nucleus, by reacting them with a perfluoroalkyl monoiodide having 3-12 carbon atoms in the molecule at about 200-350 DEG C. Examples describe the action of perfluoroheptyl iodide on copper phthalocyanine, thioindigo, pyranthrone, niolanthrone and dichloroisoviolanthrone. Alternatively dye intermediates may be perfluoroalkylated before conversion into dyes. The products may be used for colouring polytetrafluoroethylene. Thus a film of "Teflon" (Registered Trade Mark) may be dyed or printed with a solution of the dye in a fluorinated solvent and then heated to its transition temperature (324 DEG C.) to enable it to absorb the dye. Alternatively printing may be affected with heated type, maintained at about 350 DEG C., on a "Teflon" film uniformly coated with the dye (the unabsorbed portions of which are subsequently dissolved off) or having a thin sheet material coated with the dye interposed between it and the heated type, the pressure of which causes the dye to migrate into the film.
GB24567/56A 1955-08-12 1956-08-10 Process of perfluoroalkylating aromatic compounds Expired GB840725A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US840725XA 1955-08-12 1955-08-12

Publications (1)

Publication Number Publication Date
GB840725A true GB840725A (en) 1960-07-06

Family

ID=22182712

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24567/56A Expired GB840725A (en) 1955-08-12 1956-08-10 Process of perfluoroalkylating aromatic compounds

Country Status (1)

Country Link
GB (1) GB840725A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206951A2 (en) * 1985-05-22 1986-12-30 Rhone-Poulenc Chimie Process for the perfluoroalkylation of aromatic derivatives
GB2291655A (en) * 1994-07-19 1996-01-31 Secr Defence Oil and water repellent dyestuffs
US5981422A (en) * 1993-07-08 1999-11-09 Exxon Research And Engineering Co. Fluorous multiphase system
EP1572284A2 (en) * 2002-12-04 2005-09-14 Lake Region Manufacturing, Inc. Marked guidewires

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0206951A2 (en) * 1985-05-22 1986-12-30 Rhone-Poulenc Chimie Process for the perfluoroalkylation of aromatic derivatives
EP0206951A3 (en) * 1985-05-22 1987-03-11 Rhone-Poulenc Specialites Chimiques Process for the perfluoroalkylation of aromatic derivatives
US5981422A (en) * 1993-07-08 1999-11-09 Exxon Research And Engineering Co. Fluorous multiphase system
GB2291655A (en) * 1994-07-19 1996-01-31 Secr Defence Oil and water repellent dyestuffs
GB2291655B (en) * 1994-07-19 1998-06-10 Secr Defence Dyed and waterproofed fabrics and dyestuffs used in their preparation
EP1572284A2 (en) * 2002-12-04 2005-09-14 Lake Region Manufacturing, Inc. Marked guidewires
EP1572284A4 (en) * 2002-12-04 2006-12-27 Lake Region Mfg Inc Marked guidewires

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